Friday and Saturday
It is a cliché of the high school movie that the social structure is rigid, and it is almost impossible to change your status. That once you are classified as a nerd, a jock, a stoner, or a popular kid, you are locked into that status for four years barring something like getting super powers. As a nerd and social outcast, I had always hoped that this wasn't true, but as my senior year came to an end, I had pretty much accepted my lack of social status and hoped that I could start fresh in college.
My marginal position in the pecking order at North High School was not surprising on one hand—I was valedictorian, editor of the school newspaper, shy and socially awkward—and my one attempt to ask a girl out on a date in sophomore year was met by stunned silence and laughter, followed by days of giggling and pointing by most of my classmates. On the other hand, my older sister Sarah was beautiful, the most popular girl in her class, and dominated the social life of the school when she was a senior. If I had been a different person, I probably could have ridden to social acceptability on her coat tails. But when she was a senior, I was just a lowly freshman, small, skinny and shy, and never capitalized on her status in any way.
At the end of my junior year, I had the late growth spurt that my dad always promised, but which I never believed would happen. I grew 6 inches, and once I got over the pain, I started to swim a lot in our pool and at the gym. As a result, the little scrawny freshman became a 6'1", reasonably in shape, senior. But it was as if the three prior years had created a lens that prevented anyone from seeing me as anything but what I had always been. And one other thing—when you are a teenaged boy who has had zero luck with girls, and a laptop, and minimal parental supervision, you watch a lot of porn. Based on that, I could tell that my male equipment was, to say the least, fairly substantial. But I could not walk around school with my cock hanging out, so it didn't help me charm the ladies.
Despite my physical changes, I remained introverted and utterly lacking in confidence. I was afraid of girls, and could hardly speak to any of them, and the prettier they were, the more I feared them. Of course, in reality, the really pretty ones didn't even know I existed. Instead, I kept to myself and my two close friends, Fred and Gina. Yes, Gina was a girl, but she and I had been friends forever, and she didn't really do anything to act like the other girls. She wore baggy clothing, no makeup and got her hair cut at the same barber that I did. None of had been on a date, or to a big high school party. Instead, we spent time together, doing things like math league and science fairs, talking, playing video games and on the Internet, pretending that was enough for us, and what everybody else seemed to be doing for "fun," like drinking, smoking weed, dating or going to parties, was beneath us.
It was the end of my senior year, late on the afternoon of the Friday before Memorial Day weekend. I had just returned home from the coffee shop where I had been hanging out with Gina. We had a long discussion about a British TV show that we both liked, but never agreed about, and after that discussion petered out, we left, with vague plans to hang out over the long weekend. There was, I had heard, a huge party that night at a football player's house, but as usual, I was not invited, and had convinced myself that I didn't care to waste time with the morons in my class.
Instead of getting ready to go out, I was, as I often was, in my room, wasting time on my computer. I was in all AP classes and had taken the exams earlier in May, so the next month of school before graduation was going to be pretty light—a few fun projects, some final newspaper things, including passing the reins to next year's staff, and a few easy finals. And writing my graduation speech, in which I was planning on ripping my classmates for the way they had excluded me and my fellow nerds and other social pariahs.
I looked out my window to our pool and could see Sarah, home from college, and three of her friends, Ariel, Beth and Cara, standing outside the pool in their bathing suits, drinking beers and laughing. This had been one of my truly guilty pleasures over the years, watching a parade of hot girls swimming outside my window. My sister's friends were always the best looking girls in the school, and I admit to having jerked off more than once while watching them cavort in the pool. I remember once in ninth grade even seeing a girl's bikini top come off, which kept my fantasy world going for weeks.
I kept watching the girls out my window. Ariel, almost as tall as me, blonde and lightly tanned, with broad shoulders from her volleyball playing and clearly intense workouts, nice sized breasts being held up by her patterned, multicolored, bikini top, and long, athletic legs. Beth, shorter, with dark curly hair and olive skin, wearing a navy blue one piece suit that barely contained her exceptionally large tits, and which was cut high on the leg, showing off her strong gymnast's thighs. And Cara, nearly as tall as Ariel, skinny and pale, with long light brown hair that reached down to her incredible ass, which was displayed alluringly by the yellow thong style bikini she was wearing, and which was crowned with an ornate lower back tattoo. I realized that my hand had reached inside my gym shorts and that I was stroking my hardening cock. As I had so often done during the past few years, I moved to my bed, pulled down my shorts and began to jerk off in earnest.
When the door opened.
I screamed, tried to cover myself with the blanket and saw my sister, with a shocked look on her face.
"Jack-what the fuck are you doing?" she yelled.
"None of your damned business," I cleverly responded, "and don't you know how to knock?"
"I was coming to ask whether you wanted to come out for a swim with us, and I didn't expect that you were whacking off," she replied.
"Well, I kinda expected some privacy," I responded.
Now that the moment of total embarrassment had passed, and I was back in my shorts, rather than leave me alone, Sarah sat down on the edge of my bed and looked at me. We had actually always been pretty close, despite our different personalities, and I could see some concern on her face. She was a lot like our mom, and after Mom died a few years before, Sarah really tried to be there for me, even checking in on me regularly from college, which was especially helpful because Dad had reacted to Mom's death by throwing himself into his law practice and rarely was home. And when he was home, he really didn't pay much attention to what Sarah and I were doing.
"Jack," Sarah asked, in a motherly way, "do you do this a lot?"
My faced reddened and I nodded.
"You've never had a girlfriend, have you?"
I shook my head.
"And are you a--"
I interrupted her before she could finish. "Yes, I'm a virgin," I spat out, "A fucking 18 year old virgin. I haven't even kissed a girl, unless you count once in 6th grade on a dare, and I don't."
Sarah's face fell. "That shouldn't be. I mean, you have turned into kind of a hot guy, and from what I saw, your, um, is kinda--"
